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Sex pheromone of the american cockroach,Periplaneta americana

Isolation and structure elucidation of periplanone-B

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Abstract

The sex pheromone of the American cockroach,Periplaneta americana, consists of two compounds, which we have named periplanone-A and periplanone-B. The two compounds can be isolated from fecal material in a ratio of 1∶10, and periplanone-B can also be isolated from intestinal tracts. A total amount of 200 μg of periplanone-B has been isolated from both fecal material and alimentary tracts. By means of gas chromatography-mass spectrometry, hydrogenation, infrared analysis, and NMR analysis, we were able to identify periplanone-B as (1Z,5E)-1,10(14)-diepoxy-4(15),5-germacradien-9-one. The overall structure was confirmed by comparison with a synthetic, biologically active epimer of periplanone-B.

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Authors and Affiliations

  1. Central Laboratory TNO, Delft, The Netherlands

    C. J. Persoons, P. E. J. Verwiel, E. Talman & F. J. Ritter

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  1. C. J. Persoons
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  2. P. E. J. Verwiel
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  3. E. Talman
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  4. F. J. Ritter
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Persoons, C.J., Verwiel, P.E.J., Talman, E. et al. Sex pheromone of the american cockroach,Periplaneta americana . J Chem Ecol 5, 221–236 (1979). https://doi.org/10.1007/BF00988237

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  • DOI: https://doi.org/10.1007/BF00988237

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